Cesium Fluoride Catalyzed Trifluoromethylation of Esters, Aldehydes, and Ketones with (Trifluoromethyl)trimethylsilane Rajendra P. Singh Ganfeng Cao Robert L. Kirchmeier Jean'ne M. Shreeve 10.1021/jo982494c.s001 https://acs.figshare.com/articles/journal_contribution/Cesium_Fluoride_Catalyzed_Trifluoromethylation_of_Esters_Aldehydes_and_Ketones_with_Trifluoromethyl_trimethylsilane/3717339 The low reactivity of carboxylic esters toward (trifluoromethyl)trimethylsilane (TMS−CF<sub>3</sub>) was investigated. A universal cesium fluoride catalyzed procedure for nucleophilic trifluoromethylation was developed. At room temperature (25 °C), with catalytic amounts of cesium fluoride, carboxylic esters were found to react to give the silyl ether intermediates, which afforded the trifluoromethyl ketones after hydrolysis. Sulfonic, sulfinic, and selenic esters also show good reactivity, giving novel trifluoromethylated compounds. The trifluoromethylation method was also applied to aldehydes and ketones, which were transformed to trifluoromethyl silyl ether intermediates and afforded trifluoromethylated alcohols in excellent yields after acid hydrolysis. Ethylene glycol dimethyl ether was used as solvent for solid or high boiling substrates, and benzonitrile was used for the low boiling substrates. 1999-03-31 00:00:00 TMS Ethylene glycol dimethyl ether novel trifluoromethylated compounds Cesium Fluoride Catalyzed Trifluoromethylation trifluoromethylation carboxylic esters reactivity silyl ether intermediates cesium fluoride substrate ketone trifluoromethyl silyl ether intermediates hydrolysis